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  • About Us

    About Us

Why Choose Jolly Roger Sailing?

Your Training is our priority!

We always try to match the needs of individual clients with the courses we teach. We specialise in Shorebased courses and can work with you to ensure your learning journey is a positive and fun experience.

Our Experience is your Peace of Mind

Roger is a fully qualified teacher and a Yachtmaster Instructor. He has sailed over 40000 miles offshore. Other instructors we may use are of high quality and have a vast amount of experience Sailing Offshore.  Many have skippered in Sail Training vessels in events such as the Tall Ships Races. Rest assured your instructor will have been there are done it! and wants to pass it on to you!

Support from our friends and the team.

Everyone who takes part in one of course has access to a dedicated database of exercises and resources for you to dip into. Some may have been developed using resources specific to the area you sail in.  During your course you will be invited to join a WhatsApp group with all the students you are studying with, here you can share your homework ask questions and get feedback from your instructor on any self-study tasks.  Finally,  all students are invited to join Friends of Jolly Roger Sailing Facebook Group, a closed group of offshore sailors from Day Skippers to Yachtmaster examiners who are there to give you continued advice to help you stay safe on the water.

Jolly Roger Sailing

Jolly Roger Sailing was set up in 2016 as an RYA shore based teaching centre and sailing school. The aim of the company is to give excellent, value for money, shore-based RYA training in the Southampton Waterside area, the New Forest and beyond.

The Principal Instructor

Roger Drewery is an RYA Qualified instructor who has been a teacher for 20 years, working in a range of schools. His sailing experience goes back to his school days. His first experience of offshore sailing was on the OYC ketch Spirit of Boadicea, for 2 weeks, sailing from Ipswich to the Channel Islands and back. After this he was hooked. Roger sailed as a Bosun and Mate with the Ocean Youth Club, including taking part in Tall Ships races. In 1992 Roger raced across the Atlantic in the 500th anniversary of Columbus Race, on board the OYC ketch Lady Beaverbrook.

​For many years Roger has volunteered, as a mate and skipper, for Adventures Offshore, on board 50ft Oyster Ketches given young adults unforgettable experiences. He has worked with a variety of crews of various age ranges, many of whom return to sail again and some have taken up afterguard positions.

​Over the years his passion for sailing has grown into a desire to combine teaching and sailing. In early 2016 Roger decided to leave education and set up Jolly Roger Sailing. His impressive experience in both teaching and sailing allows him to make courses active and interesting, whether you are at the beginning of your sailing journey or more advanced.

The Future

Within the next few years Jolly Roger Sailing plans to move into its own premises in the waterside area and, with acquisition of a suitable vessel, start to offer practical courses to complement its shore-based work.


Roger Drewery

Roger Drewery